Water → 4-(4-Aminomethylbenzyl)-nitrobenzene

HRID 2121028Notes

Reaction equation

HRID 2121028 reaction equation
[N:1]([CH2:4][C:5]1[CH:20]=[CH:19][C:8]([CH2:9][C:10]2[CH:15]=[CH:14][C:13]([N+:16]([O-:18])=[O:17])=[CH:12][CH:11]=2)=[CH:7][CH:6]=1)=[N+]=[N-].O.C1(P(C2C=CC=CC=2)C2C=CC=CC=2)C=CC=CC=1>O1CCCC1>[NH2:1][CH2:4][C:5]1[CH:20]=[CH:19][C:8]([CH2:9][C:10]2[CH:15]=[CH:14][C:13]([N+:16]([O-:18])=[O:17])=[CH:12][CH:11]=2)=[CH:7][CH:6]=1

Participants

5

Reactant 3

HCID 962WaterHCID 11776TriphenylphosphineHCID 218770044-(4-Azidomethylbenzyl)-nitrobenzene

Product 1

HCID 218767314-(4-Aminomethylbenzyl)-nitrobenzeneYield 79%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

A solution of 4-(4-azidomethylbenzyl)-nitrobenzene (5.835 g) in tetrahydrofuran (175 mL) was treated with water (0.43 mL) and triphenylphosphine (6.45 g, 1.1 eg). The mixture was stirred at room temperature for 18 hours, and the solvent was evaporated. The residue was suspended in water, and suspension madeacidic by the dropwise addition of hydrochloric acid to about pH 1, then extracted with diethyl ether (3×). The aqueous phase was made alkaline with 50% aqueous sodium hydroxide, extracted with dichloromethane (3×) to afford a crude brown oil (5.66 g). Chromatography on silica gel, eluting with dichloromethane/methanol/ammonium hydroxide, gave 4-(4-aminomethylbenzyl)-nitrobenzene (3.91 g, 79%) as a yellow solid.

Workup

  1. customthe solvent was evaporated
  2. additionsuspension madeacidic by the dropwise addition of hydrochloric acid to about pH 1
  3. extractionextracted with diethyl ether (3×)
  4. extractionextracted with dichloromethane (3×)
  5. customto afford a crude brown oil (5.66 g)
  6. washChromatography on silica gel, eluting with dichloromethane/methanol/ammonium hydroxide

Sources & evidence

ORD record
ord-087d3cefe03648a5a5be150731c1a37f
Source dataset
uspto-grants-2004_02
Patent number
US06693200B2

Reaction notes

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